Framing nails are traditionally sized by pennies, rather than length or wire gauge as is the case with screws. Modern hardware is labeled some what differently with nails being sized by a number, followed by a "d," although the size corresponds to the old penny sizing. An 8d nail is considered sufficient for most toenailing, although a 16d allows the nail to be started further from the edge of the board, lessening the likelihood of a split. Use the longest nail possible for the strongest joint.
Position the nail at least 3/4 inch from the bottom edge of the board you are nailing through. The higher up you start it, the better the joint and the less the likelihood of splitting. Drive the angle in at about a 30-degree angle to the board you are nailing through. This will place the nail close to the center of the board's edge when it pierces into the second board.
Set the tip of the nail against the board at the desired height and running into the face of the board at a 90-degree angle. Hold the nail between the thumb and first two fingers of the non-dominant hand. Strike the hammer firmly against the nail's head to drive the point into the board. Tap the nail upward until the head is almost against the face of the board, then drive it down on the angle through the top board until the head is flush with the face of the board.
As previously mentioned, one use for toe nails is the attachment of ceiling joists to roof caps. Other places that toenails are useful include attaching twisted lumber. Another use is mounting floor boards and decking that reach the support below, but do not reach its center, requiring an angled fastener. A toe nail driven in from the opposite direction can be used to correct a board that has been misaligned by a hastily driven toenail.